Raised in Bakersfield, Sakuragi played college basketball at University of California, Los Angeles (UCLA), and was a member of their national championship team in 1994–1995. On the NCAA championship team in his freshman year, Sakuragi was named the team's most valuable freshman along with Toby Bailey.[1] He was named to the All-Pac-10 first team during his sophomore and senior seasons,[2] and was also named the Bruins' co-most valuable player both years as well.[3] He averaged 14.2 points per game in his four-year career at the school. He was selected by the Vancouver Grizzlies in the 2nd round (56th pick) of the 1998 NBA Draft where he played one season.[4]

Sakuragi played the next two years for teams in Las Vegas and France and summer-league teams in Puerto Rico and the Philippines.[5] In 2001, he moved to Japan to play for the Aisin Seahorses of the JBL Super League, averaging 21.5 points and 11.6 rebounds per game in 2006.[4]

Sakuragi's application to become a Japanese citizen cleared on July 2, 2007, and he changed his name from J. R. Henderson to J. R. Sakuragi.[4][6] He chose his new name for two reasons: firstly, he thought a Japanese name would speed up the naturalization, and secondly for the Japanese sakura cherry blossoms. It also corresponded to the name of Hanamichi Sakuragi, the protagonist of the popular basketball manga Slam Dunk.[5]

To comply with Japanese naturalization requirements, Sakuragi taught himself to read, speak and write Japanese at a "rudimentary level". He plans to stay in Japan and has no intention of returning to the U.S. soon.[5]